Supporting Information. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek and Ryan E. Looper*

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1 Supporting Information Regioselective base-mediated cyclizations of mono-n-acylpropargylguanadines. Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek and Ryan E. Looper* * Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT, r.looper@utah.edu 1. Crystal Structure Report for 4m p.2 2. Representative 1 H and 13 C NMR Spectra p.5 S1

2 Crystal Structure Report for 4m (ellipsoids are shown at a 35% probability level) A colorless prism-like specimen of C 26 H 25 N 3 O 3, approximate dimensions mm x mm x mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured.ref9 WinGX A Windows Program for Crystal Structure Analysis. L. J. Farrugia, J. Appl. Crystallogr. 2012, 45, Table S1: Data collection details for rl022. Axis dx/m m 2θ/ ω/ φ/ χ/ Width/ Frames Time/s Wavelength/ Å Volt age/ kv Current/ ma Tempe rature/ K Phi Omega Omega Omega Omega Omega Omega Omega Omega Omega Phi Omega S2

3 Axis dx/m m 2θ/ ω/ φ/ χ/ Width/ Frames Time/s Wavelength/ Å Volt age/ kv Current/ ma Tempe rature/ K Omega A total of 1725 frames were collected. The total exposure time was 4.31 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a triclinic unit cell yielded a total of reflections to a maximum θ angle of (0.76 Å resolution), of which 5411 were independent (average redundancy 8.649, completeness = 100.0%, Rint = 2.64%, Rsig = 1.47%) and 4636 (85.68%) were greater than 2σ(F2). The final cell constants of a = (5) Å, b = (5) Å, c = (5) Å, α = (3), β = (2), γ = (2), volume = (9) Å3, are based upon the refinement of the XYZ-centroids of 9409 reflections above 20 σ(i) with < 2θ < Data were corrected for absorption effects using the multi-scan method (SADABS). The ratio of minimum to maximum apparent transmission was The calculated minimum and maximum transmission coefficients (based on crystal size) are and The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P -1, with Z = 2 for the formula unit, C26H25N3O3. The final anisotropic fullmatrix least-squares refinement on F2 with 295 variables converged at R1 = 3.75%, for the observed data and wr2 = 9.77% for all data. The goodness-of-fit was The largest peak in the final difference electron density synthesis was e-/å3 and the largest hole was e- /Å3 with an RMS deviation of e-/å3. On the basis of the final model, the calculated density was g/cm3 and F(000), 452 e-. Table S2. Sample and crystal data for 4m. Identification code rl022 Chemical formula C 26 H 25 N 3 O 3 Formula weight g/mol Temperature 150(1) K Wavelength Å Crystal size x x mm Crystal habit colorless prism Crystal system triclinic Space group P -1 Unit cell dimensions a = (5) Å α = (3) b = (5) Å β = (2) c = (5) Å γ = (2) Volume (9) Å 3 Z 2 Density (calculated) g/cm 3 S3

4 Absorption coefficient mm -1 F(000) 452 Table S3. Data collection and structure refinement for 4m. Theta range for data collection 2.11 to Index ranges -14<=h<=14, -14<=k<=14, - 14<=l<=14 Reflections collected Independent reflections 5411 [R(int) = ] Coverage of independent reflections 100.0% Absorption correction multi-scan Max. and min. transmission and Structure solution technique direct methods Structure solution program SHELXT-2014/9 (Sheldrick, 2014) Refinement method Full-matrix least-squares on F 2 Refinement program SHELXL-2014/6 (Sheldrick, 2014) Function minimized Σ w(f 2 o - F 2 c ) 2 Data / restraints / parameters 5411 / 0 / 295 Goodness-of-fit on F Final R indices 4636 data; R1 = , wr2 = I>2σ(I) all data R1 = , wr2 = Weighting scheme w=1/[σ 2 (F 2 o )+(0.0430P) P] where P=(F 2 o +2F 2 c )/3 Largest diff. peak and hole and eå -3 R.M.S. deviation from mean eå -3 S4

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